Total Synthesis of a Linear Tetrasaccharide Repeating Unit of Vibrio vulnificus MO6-24.

Herein, we report the total synthesis of a linear, conjugation-ready, tetrasaccharide repeating unit of Vibrio vulnificus MO6-24, which is composed of rare amino sugars such as l-quinovosamine and d-galactosamine uronic acid. The key challenges addressed here are the synthesis of rare deoxy amino sugars, installation of consecutive 1,2- cis glycosidic linkages, and late-stage oxidation. Total synthesis of the target molecule was completed via a longest linear sequence of 29 steps in an overall yield of 0.7% starting from l-rhamnose.